US6013704AExpiredUtility
Hydroxyphenyltriazines
Est. expirySep 13, 2016(expired)· nominal 20-yr term from priority
C07D 405/14C07D 405/12C08K 5/3492C08K 5/3435C07D 251/24C07D 309/06
83
PatentIndex Score
32
Cited by
20
References
17
Claims
Abstract
There are described compounds of formula A wherein r 1 and r 2 are each independently of the other 0 or 1; Y 1 to Y 9 are each independently of the others --H, --OH, C 1 -C 20 alkyl, C 4 -C 20 cycloalkyl, C 2 -C 20 -alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, --C.tbd.N, C 1 -C 5 haloalkyl, --SO 2 R', --SO 3 H, --SO 3 M, wherein M is an alkali metal, --COOR', --CONHR', --CONR'R", --OCOOR', --OCOR', --OCONHR', (meth)acrylamino, (meth)-acryloxy, C 6 -C 12 aryl; C 6 -C 12 aryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; C 3 -C 12 heteroaryl; C 3 -C 12 heteroaryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; or Q of formula I, and at least one substituent Y 1 to Y 9 must be Q ##STR1## wherein q is 0 or 1, R is a cyclic radical and R 1 and T are as defined in claim 1. The novel compounds are suitable, especially in combination with hindered amines, for the stabilisation of organic material against the damaging action of light, oxygen and heat.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A compound of formula A ##STR56## wherein r 1 and r 2 are each independently of the other 0 or 1; Y 1 to Y 9 are each independently of the others --H, --OH, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, --C.tbd.N, C 1 -C 5 haloalkyl, --SO 2 R', --SO 3 H, --SO 3 M, wherein M is an alkali metal, --COOR', --CONHR', --CONR'R", --OCOOR', --OCOR', --OCONHR', (meth)acrylamino, (meth)acryloxy, C 6 -C 12 aryl; C 6 -C 12 aryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl; pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; or Q of formula I, and at least one substituent Y 1 to Y 9 must be Q ##STR57## wherein q is 0 or 1, and R 1 is --H, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, --COR', --COOR' or --CONHR', and T is C 1 -C 20 alkylene; C 4 -C 12 cycloalkylene; C 1 -C 20 alkylene-O--; C 2 -C 50 alkylene that is interrupted one or more oxygen atoms and/or substituted by one or more hydroxy groups; --CO--; --SO 2 --; phenylene; phenylene substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; biphenylene; or biphenylene substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen, it being possible for T, in place of hydrogen, to be substituted by one or more substituents R x that are independent of one another, and R is C 4 -C 12 cycloalkyl, C 4 -C 12 cycloalkenyl, C 6 -C 15 bicycloalkyl, C 6 -C 15 bicycloalkenyl or C 6 -C 15 tricycloalkyl, each of which may be interrupted by one or more oxygen atoms, or is naphthyl or biphenyl and, in the case where q is 1, additionally includes phenyl, it being possible for R, in place of hydrogen, to be substituted by one or more substituents R x that are independent of one another, and R x is C 1 -C 20 akyl, C 2 -C 20 alkenyl, C 4 -C 12 cycloalkyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, hydroxy, halogen, C 1 -C 5 haloalkyl, --COOR', --CONHR', --CONR'R", --OCOR', --OCOOR', --OCONHR', --NH 2 , --NHR', --NR'R", --NHCOR', --NR"COR', --NH(meth)acryl, --O(meth)acryl, --CN, ═O, ═NR'; C 6 -C 12 aryl, or C 6 -C 12 aryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; and R' and R" are each independently of the other --H; C 1 -C 20 allyl; C 4 -C 12 cycloalkyl; C 6 -C 12 aryl; C 6 -C 12 aryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl; or pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; with the exception of the compound 2,4-bisphenyl-6-(4-[3-benzoyloxy-2-hydroxypropyloxy]-2-hydroxyphenyl)-1,3,5-triazine.
2. A compound according to claim 1 of formula A1 ##STR58## wherein r 1 and r 2 and the substituents Y 1 to Y 9 are as defined in claim 1.
3. A compound according to claim 2, wherein Y 1 is Q; Y 2 is H, C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl, C 7 -C 20 aralkyl, C 1 -C 5 haloalkyl or --SO 2 R'; Y 3 is H; Y 4 to Y 9 are each independently of the others --H, --OH, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, --C.tbd.N, C 1 -C 5 haloalkyl, --SO 2 R', --SO 3 H, --SO 3 M, --COOR', --CONHR', --CONR'R", --OCOOR', --OCOR', --OCONHR', (meth)acrylamino, (meth)acryloxy, C 6 -C 12 aryl; C 6 -C 12 aryl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl; or pyridinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thiophenyl, quinolinyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; and Y 5 and Y 9 additionally include Q; Q being a radical of formula (I) ##STR59## wherein q is 0 or 1, and R 1 is --H, C 1 -C 20 alkyl, C 4 -C 12 cycloalkyl, --COR', --COOR' or --CONHR'; T is C 1 -C 20 alkylene; C 4 -C 12 cycloalkylene; C 1 -C 20 alkylene-O--; C 2 -C 50 alkylene that is interrupted by O and/or substituted by OH; --CO--; --SO 2 --; phenylene; or phenylene substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; R is C 4 -C 12 cycloalkyl, C 4 -C 12 cycloalkenyl, C 6 -C 15 bicycloalky, C 6 -C 15 bicycloalkenyl or C 6 -C 15 tricycloalkyl, each of which may be interrupted by one or more oxygen atoms, or is naphthyl or biphenyl and, in the case where q is 1 and T is other than --CO--, additionally includes phenyl, it being possible for R in the said definitions to be substituted by R x ; R x is C 1 -C 12 alkyl, C 2 -C 20 alkenyl, C 1 -C 4 alkoxy, hydroxy, halogen, C 1 -C 5 haloalkyl, --COOR', --CONHR', --CONR'R", --OCOR', --OCOOR', --OCONHR', --NH(meth)acryl, --O(meth)acryl, --CN, ═O, ═NR'; phenyl, or phenyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; and R' and R" are each independently of the other C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, phenyl, or phenyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen.
4. A compound according to claim 3, wherein r 1 and r 2 are 0, and Y 4 and Y 7 are each independently of the other --H, --OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 2 -C 20 alkenyloxy, halogen, C 1 -C 5 haloalkyl or (meth)acryloxy; Y 5 and Y 8 are each independently of the other --H, --OH, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 20 -alkoxy, C 4 -C 12 cycloalkoxy, C 3 -C 20 alkenyloxy, C 7 -C 20 phenylalkyl, halogen, C 1 -C 5 haloalkyl, --SO 2 R', --SO 3 H, --SO 3 M, --OCOOR', --OCOR', --OCONHR', (meth)acrylamino, (meth)acryloxy, phenyl; phenyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN and/or by halogen; or Q; wherein in Q of formula (I) R 1 is H; T is C 1 -C 6 alkyl and R is C 4 -C 12 cycloalkyl, R x -substituted C 4 -C 12 cycloalkyl, phenyl, R x -substituted phenyl, or C 5 -C 12 cycloalkenyl, C 6 -C 15 bicycloalkyl or C 6 -C 15 tricycloalkyl, each of which may be interrupted by one or more oxygen atoms and/or substituted by R x ; R x is C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and Y 6 and Y 9 are H or C 1 -C 12 alkyl.
5. A compound according to claim 1 of one of the formulae A2, A3, A4, A5, A6, A7 and A8 ##STR60## in which formulae Y 5 and Y 8 are each independently of the other --OH, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 3 -C 20 alkenyloxy, C 7 -C 20 phenylalkyl, halogen, C 1 -C 5 haloalkyl, --SO 2 R', --SO 3 H, --SO 3 M, --OCOOR', --OCOR', --OCONHR', (meth)acrylamino or (meth)acryloxy and the substituents Q 1 to Q 3 include the meanings defined for Q.
6. A compound according to claim 5 of one of the formulae A2, A3, A4, A5, A6, A7 and A8, wherein Q 1 , Q 2 and Q 3 are identical and Y 5 and Y 8 are identical.
7. A stabiliser mixture comprising (a) a compound of formula A according to claim 1 and (b) at least one 2,2,6,6-tetraalkylpiperidine derivative, or a salt thereof with any desired acid or a complex thereof with a metal.
8. A composition comprising 1) an organic material susceptible to damage by light, oxygen and/or heat, and 2) as stabiliser at least one compound according to claim 1.
9. A composition according to claim 8, wherein component 1) is an organic polymer.
10. A composition according to claim 8, wherein component 1) is a synthetic polymer.
11. A composition according to claim 8, wherein component 1) is a polyolefin or a surface-coating binder based on acrylic, alkyd, polyurethane, polyester or polyamide resin or correspondingly modified resins, a photographic material, a cosmetic or a sun cream.
12. A composition according to claim 8 comprising, in addition to components 1) and 2), further customary additives.
13. A composition according to claim 8 comprising from 0.01 to 10% by weight of component 2), based on the weight of the composition.
14. A method of stabilising organic material against damage by light, oxygen and/or heat, wherein a compound according to claim 1 is mixed with that material.
15. A polymer protected against damage by light, oxygen and/or heat in accordance with the method of claim 14.
16. A surface coating protected against damage by light, oxygen and/or heat in accordance with the method of claim 14.
17. A photographic material protected against damage by light, oxygen and/or heat in accordance with the method of claim 14.Cited by (0)
No later patents cite this yet.
References (0)
No backward citations on record.